We sipped complimentary glasses of wine on the flight and then settled into a penthouse suite at Le Place D’Armes Hotel, which cost $640 a night. We hit Joe Beef and tried the horse with artichokes and pecorino, plus just about everything else on the menu—a habit of ours when we can’t decide what not to get. Around 1 a.m., we rolled into New City Gas, a warehouse nightclub just outside the Old Port, totally obliterated. My cousin had booked us a booth, and we ordered bottle service—the Grey Goose, Hendricks, Patrón and Moët were flowing. We stayed until nearly 6 a.m., dancing to house music and trying to pick up girls (alas, none of us got lucky). We gorged and guzzled our way through the rest of the weekend, eating ridiculously decadent cronuts from a pâtisserie, smoked meat sandwiches from Schwartz’s, fondue from an amazing Old Montreal restaurant called Bistro Marché de la Villette. We uncorked bottle after bottle of Amarone as we went. The pinnacle of the weekend was two hours on a closed racetrack behind the wheel of a $200,000 dark blue Lamborghini Gallardo. I tried to redline it—it tops out around 310 kilometres per hour—but the rental guy talked me down around 220. We were gone for only 48 hours, but it felt like 10 weekends packed into one.

As brash and disgusting as this kind of macho, bragging, excess is, the undertone of the entire piece is longingly defensive. This person seems very aware that their choices are willfully selfish and that eventually the high will wear off. They make a ton of money, are lucky beyond belief to have zero expenses, and spends it all on experiences that can’t measure up to what they hoped. Eventually they’ll have to change and find a way to develop a healthy relationship with their money and their choices. They spend the piece trying to convince themselves that what they’re doing now is actually worth it. This man doesn’t feel nearly guilty enough.

. . .

More than the entertainment and feelings of jealousy, this piece actually got me thinking about my own financial situation of late. I started a new job a few months ago. Previously I was making $35,000 per year, decent pay for retail. And I currently make $45,000 per year at a desk job. That’s a decent raise. It’s helped my financial situation immensely. But I’ve been questioning: when should I start to feel guilty about my income?

I am not rich. I still make below median income, but compared to before, my life feels so extravagant. At $35,000 per year, I could afford my life, but just barely. Rent, bills, student loans, a tiny bit of spending money, and a bit of a credit card balance that I couldn’t shake were using 100% of my income. I never felt like I had to truly worry about being able to afford the necessities, but sometimes rent had to wait until the next paycheck. Sometimes $20 of groceries had to go on the credit card until the next paycheck. The bank balance would reliably bounce all the way down before climbing back up a bit again. This is how I’ve lived my entire adult life. As long as I’ve had a job and paid for my own things, I’ve never had money that didn’t need to be spent on something essential. Or I’ve always had consequences when I didn’t spend that money on the essential thing.

Again, $45,000 per year is not rich. But even having a little bit of money left over feels rich. And that feels guilty.

It feels guilty because it feels like I cheated. My previous job was hard, physically and mentally strenuous. I worked alongside my team and suffered with them and we felt like we earned (more than) our wages through our toil. My job now? It's not very hard. It's skilled, but it's not strenuous. I got the job because I'm uniquely qualified, but it does involve anything that I would describe as toil. Mentally and physically, my work demands less of me than ever before, and I'm making more money doing it. That feels like cheating. It makes my increased earnings feel unearned.

I mostly know that this is a lie. It's a mechanism my brain adopts to reconcile and understand how my life has changed. I know intellectually that more income shouldn't demand more of my energy as a price. That is one of capitalism's lies. But another one of its lies is that more income is always earned, that accruing wealth is a result of your merits.

Part of me is grateful for my guilt response. I want to be sensitive to this reality of capitalism and the way money distorts your thinking. That one day I could start earning enough that I should feel guilty about it. Where is that line? If I haven't reached it yet at $45,000 per year, will I at the median income? Maybe upper middle class? Is it $130,000 per year?

I hope that I always feel valuable, and never let my employer convince me that I'm not worth my income. But I'll always want to balance that with the knowledge that at some point, you can be too rich.